Methanol → HCID 86686984, compound

HRID 1402117Notes

Reaction equation

HRID 1402117 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=O)[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][C:40]2[N:44]3[CH:45]=[C:46]([O:49][C@H:50]4[C:59]5[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=5)[C@@H:53]([NH2:60])[CH2:52][CH2:51]4)[CH:47]=[CH:48][C:43]3=[N:42][N:41]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C.CO>CN(C=O)C.C(Cl)Cl>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][C:40]2[N:44]3[CH:45]=[C:46]([O:49][C@H:50]4[C:59]5[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=5)[C@@H:53]([NH:60][C:5]([NH:6][C:7]5[N:8]([C:16]6[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=6)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=5)=[O:4])[CH2:52][CH2:51]4)[CH:47]=[CH:48][C:43]3=[N:42][N:41]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 866869834-[6-((1R,4S)-4-Amino-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86686984HCID 86686984, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A dark brown solution of (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Synthetic Communications, 2009, 39, 3999-4009, which is incorporated herein by reference in its entirety; 162 mg, 0.401 mmol), Intermediate 22b (174 mg, 0.364 mmol) and DIPEA (0.079 mL, 0.455 mmol) in DMF (5 mL) was stirred at 100° C. for 3 h. The solution was cooled to RT, concentrated in vacuo, suspended in water (10 mL) and extracted with DCM (2×10 mL). The combined organics were passed through a hydrophobic frit and concentrated in vacuo to leave a brown gum. FCC, using 2-6% MeOH in DCM, gave the title compound as an off-white solid (155 mg, 58%). LCMS (Method 3): Rt 4.16 min, m/z 733 [MH+].

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with DCM (2×10 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a brown gum

Sources & evidence

ORD record
ord-2d59d840d6f34ef18b67bf665e6ac33a
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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